FR2362104A1 - PROCESS FOR PREPARING RESORCINOL - Google Patents
PROCESS FOR PREPARING RESORCINOLInfo
- Publication number
- FR2362104A1 FR2362104A1 FR7725151A FR7725151A FR2362104A1 FR 2362104 A1 FR2362104 A1 FR 2362104A1 FR 7725151 A FR7725151 A FR 7725151A FR 7725151 A FR7725151 A FR 7725151A FR 2362104 A1 FR2362104 A1 FR 2362104A1
- Authority
- FR
- France
- Prior art keywords
- resorcinol
- subjected
- stage
- products
- aromatic hydrocarbon
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 title abstract 6
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000006227 byproduct Substances 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 2
- 238000003776 cleavage reaction Methods 0.000 abstract 2
- 230000007017 scission Effects 0.000 abstract 2
- UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 abstract 1
- IROSBXFYXRIPRU-UHFFFAOYSA-N 1,3-bis(2-hydroperoxypropan-2-yl)benzene Chemical compound OOC(C)(C)C1=CC=CC(C(C)(C)OO)=C1 IROSBXFYXRIPRU-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- -1 carbinol hydroperoxide Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
L'invention concerne un procédé pour préparer du résorcinol. On soumet à un premier stade de pretraitement un produit d'oxydation du m-diisopropylbenzène constitué de dihydroperoxyde de m-diisopropylbenzène et comme sous-produits d'hydroperoxyde de carbinol m-substitué et/ou de dicarbinol m-substitué, avec du peroxyde d'hydrogène, en présence d'un catalyseur acide, dans un système hétérogène d'un solvant hydrocarboné aromatique aqueux, dans des conditions ne provoquant pratiquement pas de clivage acide et en éliminant l'eau formée comme sous-produit sous forme d'un azéotrope avec l'hydrocarbure aromatique et dans un second stade on soumet le produit réactionnel prétraité à un clivage acide pratiquement en l'absence de peroxyde d'hydrogène. L'invention permet en particulier d'obtenir des rendements améliorés en résorcinol en évitant la formation de sous-produits réactifs.The invention relates to a process for preparing resorcinol. An oxidation product of m-diisopropylbenzene consisting of m-diisopropylbenzene dihydroperoxide and as by-products of m-substituted carbinol hydroperoxide and / or m-substituted dicarbinol, with d peroxide is subjected to a first stage of pretreatment. 'hydrogen, in the presence of an acid catalyst, in a heterogeneous system of an aqueous aromatic hydrocarbon solvent, under conditions causing virtually no acid cleavage and removing the water formed as a by-product as an azeotrope with the aromatic hydrocarbon and in a second stage the pretreated reaction product is subjected to acid cleavage substantially in the absence of hydrogen peroxide. The invention makes it possible in particular to obtain improved yields of resorcinol while avoiding the formation of reactive by-products.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51097680A JPS5852972B2 (en) | 1976-08-18 | 1976-08-18 | Method for producing divalent phenols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2362104A1 true FR2362104A1 (en) | 1978-03-17 |
| FR2362104B1 FR2362104B1 (en) | 1980-05-16 |
Family
ID=14198697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7725151A Granted FR2362104A1 (en) | 1976-08-18 | 1977-08-17 | PROCESS FOR PREPARING RESORCINOL |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4283570A (en) |
| JP (1) | JPS5852972B2 (en) |
| CA (1) | CA1097375A (en) |
| DE (1) | DE2737302C3 (en) |
| FR (1) | FR2362104A1 (en) |
| GB (1) | GB1539833A (en) |
| IT (1) | IT1084165B (en) |
| NL (1) | NL174719C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2405231A1 (en) * | 1977-10-08 | 1979-05-04 | Mitsui Petrochemical Ind | RESORCIN PREPARATION PROCESS |
| FR2439184A1 (en) * | 1978-10-17 | 1980-05-16 | Mitsui Petrochemical Ind |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS599532B2 (en) * | 1978-05-30 | 1984-03-03 | 三井化学株式会社 | How to recover resorcinol |
| JPS6138166Y2 (en) * | 1978-11-30 | 1986-11-05 | ||
| US4288254A (en) * | 1979-07-27 | 1981-09-08 | Nl Chem Canada Inc. | Predispersed slurry of titanium dioxide |
| JPS5835135A (en) * | 1981-08-27 | 1983-03-01 | Sumitomo Chem Co Ltd | Preparation of phloroglucin |
| JPS5888356A (en) * | 1981-11-19 | 1983-05-26 | Sumitomo Chem Co Ltd | Method for producing triisopropylbenzene trihydroperoxides |
| JPS5972705A (en) * | 1982-10-20 | 1984-04-24 | Matsushita Electric Ind Co Ltd | Solenoid driving circuit |
| US4516677A (en) * | 1983-12-12 | 1985-05-14 | Burlington Industries, Inc. | Modular pallet and shipping tray |
| US5233095A (en) * | 1986-03-18 | 1993-08-03 | Catalytica, Inc. | Process for manufacture of resorcinol |
| US4861921A (en) * | 1986-03-18 | 1989-08-29 | Catalytica Associates | Process for manufacture of resorcinol |
| US4933506A (en) * | 1987-12-07 | 1990-06-12 | Mitsui Petrochemical Industries, Ltd. | Process for the production of dihydric phenols |
| US4849549A (en) * | 1987-12-22 | 1989-07-18 | Indspec Chemical Corporation | Process for preparation of resorcinol |
| US4847437A (en) * | 1987-12-22 | 1989-07-11 | Indspec Chemical Corporation | Oxidation and subsequent decomposition of dihydroperoxide |
| DE68905346T2 (en) * | 1988-02-04 | 1993-07-22 | Mitsui Petrochemical Ind | 3- (2-HYDROPEROXY-2-PROPYL) PHENOL AND METHOD FOR PRODUCING RESORCIN WITH THIS PHENOL. |
| US6350921B1 (en) | 1998-02-24 | 2002-02-26 | Indspec Chemical Corporation | Process for the production of a dihydroxybenzene and dicarbinol from diisopropylbenzene |
| US6943270B2 (en) * | 2000-03-03 | 2005-09-13 | Illa International, Llc | High selective method of producing cumene hydroperoxide, phenol and acetone in an oxidation by-product conversion process |
| EP2412695B1 (en) | 2009-03-25 | 2017-11-15 | Sumitomo Chemical Company, Limited | Method of purifying dihydroxybenzene |
| CN115583906B (en) * | 2021-07-05 | 2024-08-30 | 中国石油化工股份有限公司 | Treatment method and recycling method of m-diisopropylbenzene oxidation liquid and production method of resorcinol |
| CN115010637B (en) * | 2022-06-14 | 2023-09-19 | 万华化学集团股份有限公司 | Method for preparing m-dihydrobenzene |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2735871A (en) * | 1956-02-21 | Treatment of aralkyl hydroperoxides | ||
| US2718530A (en) * | 1950-10-05 | 1955-09-20 | Hercules Powder Co Ltd | Nitrated aromatic hydroperoxides |
| DE947309C (en) * | 1952-06-19 | 1956-08-16 | Rhone Poulenc Sa | Process for the production of hydroquinone |
| GB748287A (en) * | 1953-05-20 | 1956-04-25 | Distillers Co Yeast Ltd | Phenol production |
| BE608250A (en) * | 1960-09-17 | |||
| JPS59489B2 (en) * | 1972-11-21 | 1984-01-07 | 住友化学工業株式会社 | Decomposition method of dihydroperoxide |
-
1976
- 1976-08-18 JP JP51097680A patent/JPS5852972B2/en not_active Expired
-
1977
- 1977-08-17 IT IT26750/77A patent/IT1084165B/en active
- 1977-08-17 GB GB34515/77A patent/GB1539833A/en not_active Expired
- 1977-08-17 CA CA284,909A patent/CA1097375A/en not_active Expired
- 1977-08-17 FR FR7725151A patent/FR2362104A1/en active Granted
- 1977-08-18 NL NLAANVRAGE7709146,A patent/NL174719C/en not_active IP Right Cessation
- 1977-08-18 DE DE2737302A patent/DE2737302C3/en not_active Expired
-
1980
- 1980-01-28 US US06/115,704 patent/US4283570A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2405231A1 (en) * | 1977-10-08 | 1979-05-04 | Mitsui Petrochemical Ind | RESORCIN PREPARATION PROCESS |
| FR2439184A1 (en) * | 1978-10-17 | 1980-05-16 | Mitsui Petrochemical Ind |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2737302A1 (en) | 1978-02-23 |
| NL174719C (en) | 1984-08-01 |
| NL7709146A (en) | 1978-02-21 |
| IT1084165B (en) | 1985-05-25 |
| GB1539833A (en) | 1979-02-07 |
| JPS5323939A (en) | 1978-03-06 |
| FR2362104B1 (en) | 1980-05-16 |
| CA1097375A (en) | 1981-03-10 |
| DE2737302B2 (en) | 1981-06-19 |
| DE2737302C3 (en) | 1982-04-29 |
| JPS5852972B2 (en) | 1983-11-26 |
| NL174719B (en) | 1984-03-01 |
| US4283570A (en) | 1981-08-11 |
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